1-{[4-(4-{[(2-Oxidonaphthalen-1-yl)methylidene]azaniumyl}phenoxy)phenyl]iminiumylmethyl}naphthalen-2-olate

Abstract

The title Schiff base compound, C34H24N2O3, was prepared by a condensation reaction of bifunctional aromatic diamine (4,4′-diamino­diphenyl ether) with hy­droxy­naphtaldehyde. The asymmetric unit contains two independent mol­ecules with similar conformations. The compound contains a central oxygen bridge and two functionalized [(E)-(phenyl­iminio)meth­yl]naphthalen-2-olate units. The dihedral angles between the benzene rings linking to the central O atom are 74.64 (19) and 69.85 (18)° in the two independent mol­ecules. Intra­molecular O—H⋯O hydrogen bonding occurs between the protonated imino N atoms and deprotonated hy­droxy O atoms in both mol­ecules. In the crystal, weak C—H⋯O hydrogen bonds are observed.

Bis{4-[(2-hydroxy-5-methoxy-3-nitrobenzylidene)amino]phenyl} ether

“…(I) 4-methoxy-2-nitrophenol 66.0 (2) 4.9 (2), 4.9 (2) À177.7 (4), À177.7 (4) DICKUW (Chu & Huang, 2007) 2,4-di-tert-butylphenol 73.8 4.8, 35.5 178.2, 177.2 DICLAD (Chu & Huang, 2007) 2-(tert-butyl)-4-methylphenol 73.8 47.9, 46.3 175.2, À179.9 GIFCEG (Arafath et al, 2018) 2-methylphenol 59.5 36.0, 31.5 178.3, 179.0 HUDJEW (Lee & Lee, 2009) 4-nitrophenyl 75.7 53.0, 18.0 À174.0, 179.2 NATWEM (Khalaji et al, 2012) 2,3,4-trimethoxyphenyl 84.8 57.6, 73.1 À179.2, À175.7 PEHGOA (Kadu et al, 2013) phenyl 59.8 8.8, 6.0 À179.9, 179.8 PEHHAN (Kadu et al, 2013) 4-methoxyphenyl 60.1 5.3, 5.3 À179.3, À179.3 RIZFEM (Xu et al, 2008) 2-methoxyphenol 69.2 24.3, 24.3 À180.0, À180.0 TOWSOP (Kaabi et al, 2015) 3-(diethylamino)phenol 65.7 41.4, 30.6 À173.1, À176.5 UNUFEP (Shahverdizadeh & Tiekink, 2011) phenol 54.6 51.6, 51.6 173.5, 173.4 WEFLUQ (Krishna et al, 2012) naphthalen-2-ol 75.1/70.1 7.7, 9.9/6.1, 19.4 176.5, 177.6/-179.3, À172.9 WIGPOT (Haffar et al, 2013) naphthalen-2-ol 74.6/69.9 7.7. 9.9/19.6, 5.8 177.2, 176.3/ À172.9, À178.6…”